The Inkin' Memorial
The new first-place trophy of The Style Invitational, the weekly humor/wordplay contest of The Washington Post.
When contestants' entries are published, they are said to "get ink"; hence the name. Because many of the contest's runner-up prizes said "Loser" on them, the contestants as a community became known as the Losers. Hence the oxymoronic (or perhaps just moronic) "Winning Loser."
See this week's Style Invitational contest and many previous ones at wapo.st/StyleInv.